1,2,3,4,6,7,8,9-octahydro-3,8-dimethyl-4,9-diphenylpyrido (3,4-g)isoquininoline dihydrochloride

ABSTRACT

The title compound is useful as an anthelmintic.

Schwan.

Slates Patent [191 [75] Inventor: Thomas J. Schwan, Norwich, NY.

[73] Assignee: Morton-Norwich Products, Inc.,

Norwich, NY.

[22] Filed: Oct. 23, 1973 [2]] Appl. No.: 408,735

[52] U.S. Cl 260/286 R, 260/288 R, 260/288 P, 260/5705 P, 424/258 [51]Int. Cl C07d 39/00 [58] Field of Search 260/288 R, 288 P [451 Jan. 28,1975 [56] References Cited UNITED STATES PATENTS 3,329.68! 7/]967 Dwyer260/288 P OTHER PUBLICATIONS Chem.- Abstracts; 8th Coll. p. 228825 col.3.

Primary Examiner-D0nald G. Dams Assistant Examiner-Mary C. VaughnAttorney, Agent, or Firm-Anthony J. Franze [57] ABSTRACT The titlecompound is useful as an anthelmintic.

1 Claim, No Drawings 1 l,2,3,4,6,7,8,9-OCTAHYDRO-3,8-DlMETHYL-4,9-DIPHENYLPYRIDO (3,4-G)ISOQUININOLINE V DIHYDROCHLORIDE This invention isconcerned with the compound l,2,3,4,6,7,8,9-octahydro 3,8-dimethyl-4,9-diphenylpyrido [3,4-g1isoquinoline dihydrochloride. This compoundpossesses anthelmintic properties. When administered perorally to miceharboring Hymanolepis nana in a dose of I mg/kg b.i.d. for three days, a77% reduction in worm population is secured.

In order that this invention may be available to and understood by thoseskilled in the art, the following method for its preparation is setforth:

A. N,N-bis (l-Hydroxy-l-phenyl-2-propyl)-p-xylene-a,a-diamine A 2 l. 3neck flask was charged with 2-amino-lphenyl-l-propanol hydrochloride(l49.6 g, 0.8 mole),

terephthaldicarboxaldehyde (53.6 g, 0.4 mole), triethtween L500 ml.water and 1,500 ml. chloroform. The combined chloroform extracts weredried (MgSO and concentrated to dryness in vacuo yielding l60 g (99%).

. B'. l ,23.4.6.7,8,9-Octahydro-3-,8-dimethyl-4.9 diphenylpyrido[3,4-glisoquinoline Dihydrochloride To 960 gms of polyphosphoric acidwas introduced A (I60 g. 0.395 mole). After cautiously raising thetemperature to (steam bath) the reaction became exothermic and thetemperature rose to l30 before subsiding. Following continuous stirringovernight at ambient temperature the resulting viscous oil was pouredinto 6 l of cold tap water and the mixture was made basic with l l. of50% potassium hydroxide producing 156 gms of white solid. Thehydrochloride was prepared by suspending the free base in hot methanolwith subsequent addition of methanolic hydrogen chloride to yield 58 g(33%), mp. 344 (dec.).

Anal. Calcd. for C H N 'HClz C, 70.74; H, 6.85; N, 6.35. Found: C,71.03; H, 6.99; N, 6.17.

What is claimed:

1. l,2,3,4,6,7,8,9-Octahydro-3,8-dimethyl-4, diphenylpyrido[3,4-g1isoquinoline dihydrochloride.

